HCID 70622593, compound → HCID 70621330, compound

HRID 2398546Notes

Reaction equation

HRID 2398546 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1)([O-])=O>[Ni].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1

Participants

4

Reactant 1

HCID 70622593HCID 70622593, compound

Product 1

HCID 70621330HCID 70621330, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 12.4 g of N-(4-nitro-o-tolyl)-4-chlorophthalimide, 1.0 lt. ethyl acetate and 10 ml of an ethanolic suspension containing 6.9 g of Raney nickel is hydrogenated at 2.8 atm. and room temperature for 12 hours. It is filtered, concentrated to about half of its original volume and the precipitate formed collected, to yield the N-(4-amino-o-tolyl)-4-chlorophthalimide melting at 201°-203°. Its 4-bromo-analog melts at 208°-211°.

Workup

  1. filtrationIt is filtered
  2. concentrationconcentrated to about half of its original volume
  3. customthe precipitate formed
  4. customcollected

Sources & evidence

ORD record
ord-12b6b745af744fbcbb6828709ffe20f6
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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